JP2008222707A - Pyridyl-triazolopyrimidine derivative or its salt, harmful organism-controlling agent containing the same and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a novel harmful organism-controlling agent, e.g., which can control various harmful organisms which are of problem in an agricultural and horticultural field and harmful organisms parasitizing animals. <P>SOLUTION: The harmful organism-controlling agent contains a pyridyl-triazolopyrimidine derivative expressed by formula (I) [wherein R<SP>1</SP>expresses a substitutable alkyl, a substitutable cycloalkyl, a substitutable alkenyl, a substitutable alkynyl, a halogen, cyano, an aryl, a heterocyclic group which may be substituted with an alkyl, OR<SP>2</SP>, S(O)<SB>n</SB>R<SP>3</SP>or NR<SP>4</SP>R<SP>5</SP>, wherein R<SP>2</SP>expresses H, an alkyl, an alkenyl, an alkynyl, a haloalkyl, an alkoxyalkyl, acetyl or an aryl; R<SP>3</SP>expresses an alkyl or acetyl; R<SP>4</SP>expresses H or an alkyl; R<SP>5</SP>expresses H, an alkyl or the like; X expresses an alkyl, an alkenyl, an alkynyl, a halogen, a haloalkyl, cyano, nitro or the like; m is an integer of 1-4; n is an integer of 0-2] or its salt as an active ingredient. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a pest control agent containing a novel pyridyl-triazolopyrimidine derivative or a salt thereof as an active ingredient.

Patent Document 1 discloses the use of a triazolopyrimidine derivative having a specific chemical structure as a nematicide. However, these compounds differ in chemical structure from the compounds of the present invention. Patent Document 2 discloses a method for inhibiting or treating cancerous tumor cell proliferation and related diseases by administering an effective amount of a triazolopyrimidine derivative to a mammal. However, there is no description of the compounds of the present invention and the use of the compounds of the present invention as pest control agents.
International Publication No. WO2004 / 083383 International Publication WO2002 / 02563

  Many pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance and their use being restricted. Therefore, development of a new pest control agent with few such disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture and pests parasitic on animals is desired.

  The present inventors have made various studies on pyridyl-triazolopyrimidine derivatives in order to find better pest control agents. As a result, it was found that the novel pyridyl-triazolopyrimidine derivative has a very high control effect against pests at a low dosage, and also has safety against crops, pest natural enemies or mammals. The present invention has been completed.

  That is, the present invention relates to the formula (I):

[Wherein, R ¹ is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl, heterocyclic group optionally substituted with alkyl, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ ; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl or aryl R ³ is alkyl or acetyl; R ⁴ is hydrogen or alkyl; R ⁵ is hydrogen, alkyl, acetyl, CH ₂ CH ₂ OR ² or CH ₂ CN; A is halogen, OR ² , ^{_{S (O) n R 3,}} NR 4 R 5, cyano, alkyl, cycloalkyl, aryl, heterocyclic group, an SCH ₂ COOR ² or -CH (CN) _2; X is alkyl, alkenyl, Rukiniru, aryl, halogen, haloalkyl, cyano, ^{nitro, NR 4 R 5, S (} O) be _n R ^3, COR ² or COOR ^2; m is an integer of from 1 to 4; n is integer of 0 to 2 Provided that 7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine is excluded] -It relates to a triazolopyrimidine derivative or a salt thereof.
The present invention also relates to a pest control agent comprising a pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient, a method for controlling pests by applying them, and a method for producing them.

  The pest control agent comprising the pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests with a low dose.

When m in the formula (I) is an integer of 2 to 4, each X may be the same or different.
Examples of the halogen in formula (I) or the halogen as a substituent include fluorine, chlorine, bromine or iodine atoms. The number of halogens as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different. Further, the halogen substitution position may be any position.
The alkyl in formula (I) may be linear or branched, and specific examples thereof include C ₁ such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl. _{-6 and} the like.
Examples of cycloalkyl in the formula (I) include C _3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkenyl in the formula (I) may be linear or branched, and specific examples thereof include vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1 - like those of _{C 2-6,} such as hexenyl.
The alkynyl in the formula (I) may be linear or branched, and specific examples thereof include ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-pentene- Examples include C _2-6 such as 4-ynyl and 3-hexynyl.
Examples of the aryl in the formula (I) include C _6-10 aryl such as phenyl and naphthyl.

  The heterocyclic group in the formula (I) includes a condensed heterocyclic group in addition to a monocyclic heterocyclic group. Monocyclic heterocyclic groups include, for example, 3-membered heterocyclic groups such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl 5-membered heterocyclic groups such as pyrazolinyl, pyrazolidinyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; 6-membered heterocyclic groups such as pyranyl, pyridyl, piperidinyl, dioxanyl, oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, triazinyl Is mentioned. Among these monocyclic heterocyclic groups, a 5- or 6-membered heterocyclic group containing 1 to 4 of at least one atom selected from the group consisting of O, S and N is desirable. Examples of the condensed heterocyclic group include benzofuranyl, isobenzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothienyl, dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, Benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizylyl , Naphthyridinyl, pteridinyl, dihydrobenzoxazinyl, dihydrobenzoxazolinonyl, dihydride Benzoxadiazoles nonyl, benzothiadiazole oxa sulfonyl and the like. Among these condensed heterocyclic groups, 8 to 10-membered condensed heterocyclic groups containing 1 to 4 of at least one atom selected from the group consisting of O, S and N are desirable.

  The salt of the pyridyl-triazolopyrimidine derivative of the formula (I) includes any agriculturally acceptable salt. Examples thereof include ammonium salts such as dimethylammonium salt and triethylammonium salt; hydrochloride Inorganic acid salts such as perchlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.

  The pyridyl-triazolopyrimidine derivative of the formula (I) may have isomers such as optical isomers and geometric isomers, but the present invention includes both isomers and isomer mixtures. It is. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Depending on the type of isomer, there may be a chemical structure different from that of the formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, the scope of the present invention. It is clear that it is within.

The pyridyl-triazolopyrimidine derivative of the formula (I) or a salt thereof can be produced according to the following production methods [1] to [9] and usual salt production methods.
Manufacturing method [1]

In the production method [1], R ^1a is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, aryl or A heterocyclic group which may be substituted with alkyl; R ⁶ and R ⁷ are each independently alkyl; A, X and m are as defined above;

  In the production method [1], the compound of the formula (II) and the compound of the formula (III) are condensed to obtain the α, β-unsaturated ketone derivative of the formula (IV), and the formula (IV) The latter reaction consists of condensing the compound with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-1).

  Production Method [1] In the first half of the reaction, the compound of formula (III) can be used at a ratio of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (II). This reaction can usually be performed in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile, propionitrile and the like Nitriles; acid amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; phosphoric acid such as hexamethylphosphoramide Earth; chloroform, dichloromethane, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloroethane; and can be mixtures of these solvents. The reaction temperature is usually 80 to 200 ° C, preferably 100 to 150 ° C. The reaction time is usually 6 to 48 hours.

Production method [1] In the latter half of the reaction, the compound of formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, relative to 1 mol of the compound of formula (IV). This reaction can usually be performed in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction, for example, carboxylic acids such as acetic acid and propionic acid; alcohols such as methanol, ethanol, propanol and butanol; aromatic carbonization such as benzene, toluene and xylene. Hydrogen: aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran, dioxane; esters such as methyl acetate and ethyl acetate Nitriles such as acetonitrile and propionitrile; acid amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; Examples thereof include phosphoric acid amides such as samethyl phosphoramide; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof, among which carboxylic acids are preferable. . The reaction temperature is usually 50 to 150 ° C, preferably 80 to 120 ° C. The reaction time is usually 0.5 to 100 hours.
Manufacturing method [2]

In the production process [2], Y is halogen, and R ³ , X and m are as described above. Examples of the halogen of Y include fluorine, chlorine, bromine and iodine atoms.

  The production method [2] includes a reaction in the first half to obtain a α, β-unsaturated ketone derivative of the formula (VII) by reacting a compound of the formula (II), carbon disulfide and a compound of the formula (VI). The latter reaction consists of condensing the compound of formula (VII) with the compound of formula (V) to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-2).

  Production method [2] In the first half of the reaction, carbon disulfide and the compound of formula (VI) are used in an amount of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II). it can. This reaction can be performed in the presence of a base and a solvent. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium Ethoxide, alkali metal alkoxides such as potassium tertiary butoxide; and the like. The base can be used at a ratio of 1 to 10 equivalents, preferably 1 to 3 equivalents, per 1 mol of the compound of formula (II). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1]. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C. The reaction time is usually 6 to 48 hours.

Production method [2] In the latter half of the reaction, the compound of formula (V) can be used in a proportion of 0.8 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (VII). This reaction can usually be performed in the presence of a base and a solvent. Examples of the base include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium Alkali metal alkoxides such as ethoxide and potassium tertiary butoxide; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate; such as triethylamine and pyridine Organic bases; and the like. A base can be used in the ratio of 1-5 equivalent with respect to 1 mol of compounds of Formula (V), desirably 1-3 equivalent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the first half of the production method [1]. The reaction temperature is usually 100 to 200 ° C. The reaction time is usually 0.1 to 10 hours.
Manufacturing method [3]

In the production process [3], R ³ , X and m are as described above, and na is an integer of 1 to 2.

  In the production method [3], the compound of formula (I-2) and an oxidant are reacted in the presence of a solvent, whereby [1,2,4] triazolo [1,5-a of formula (I-3) is reacted. Pyrimidine derivatives can be produced.

Examples of the oxidizing agent used in the above reaction include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like. The solvent may be any solvent inert to the reaction, for example, halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane; ketones such as acetone and dimethyl ethyl ketone; Mention may be made of ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; carboxylic acids such as acetic acid and propionic acid; and mixed solvents thereof. An oxidizing agent can be used in the ratio of 1-3 equivalent with respect to 1 mol of compounds of a formula (I-2). The reaction temperature is usually room temperature to reflux temperature. The reaction time is usually 1 to 24 hours.
Manufacturing method [4]

In the production process [4], R ^1b is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl, alkyl which may be substituted with alkyl, OR ² or NR ⁴ R ⁵ ; R ² , R ⁴ , R ⁵ , A, X and m are as defined above.

  In the production method [4], the compound of the formula (I-3) and the nucleophile are reacted in the presence of a solvent, whereby [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.

Examples of the nucleophile include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; primary or secondary amines such as methylamine, dimethylamine and piperidine; And organometallic reagents such as bromide, ethylmagnesium bromide, and phenylmagnesium bromide; fluorinating agents such as potassium fluoride, cesium fluoride, and tetrabutylammonium fluoride; The nucleophilic reagent can be used at a ratio of 1 to 5 equivalents, preferably 1 to 3 equivalents, relative to 1 mol of the compound of formula (I-3). Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane and heptane Aliphatic ethers such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; esters such as methyl acetate and ethyl acetate; acetonitrile, propionitrile and the like Nitriles of the following; acid amides such as dimethylformamide, dimethylacetamide, N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; and mixed solvents thereof. The reaction temperature is usually −100 to 50 ° C., preferably −70 to 30 ° C. The reaction time is usually 1 minute to 48 hours.
Manufacturing method [5]

In the production method [5], R ^1c is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, aryl or alkyl. An optionally substituted heterocyclic group; R ⁸ is alkyl; A, X and m are as defined above.

  In the production method [5], the reaction of the first half to obtain the compound of the formula (IX) by reacting the compound of the formula (II) with the compound of the formula (VIII), the compound of the formula (IX) and the compound of the formula (V) The latter reaction consists of condensing the compound to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-5).

  In the first half of the reaction [5], the compound of the formula (VIII) can be used in a proportion of 0.8 equivalent to a large excess, desirably 1 to 10 equivalents, per 1 mol of the compound of the formula (II). This reaction can be performed in the presence of a base and a solvent. Examples of the base include those similar to the reaction in the first half of the above production method [2]. A base can be used in the ratio of 1-5 equivalent with respect to the compound of Formula (II), desirably 1-2 equivalent. Any solvent may be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin and petroleum benzine; ethers such as diethyl ether, dipropyl ether, dibutyl ether, tetrahydrofuran and dioxane; acid amides such as dimethylformamide, dimethylacetamide and N-methylpyrrolidinone; dimethyl Examples thereof include sulfoxides such as sulfoxide; sulfones such as sulfolane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. But among them ethers are preferred. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

Production Method [5] In the latter half of the reaction, the compound of formula (V) can be used in a proportion of 0.8 to 10 equivalents, preferably 1 to 2.5 equivalents, per 1 mol of the compound of formula (IX). This reaction can be performed in the presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction in the latter half of the above production method [1]. Among them, carboxylic acids are preferable. In addition, when Formula (IX) is a liquid at normal temperature, after the reaction in the first half of the production method [5], the reaction in the latter half of the production method [5] can be carried out without isolating the compound. The reaction temperature is usually 50 to 150 ° C, preferably 80 to 120 ° C. The reaction time is usually 0.5 to 100 hours.
Manufacturing method [6]

In the production process [6], R ^1d is halogen; R ⁹ and R ¹⁰ are each independently alkyl; X, Y and m are as described above. R ^1d halogen includes fluorine, chlorine or bromine atoms.

  In the production method [6], the compound of the formula (I-6) can be produced by the reactions (a) to (e) above. Each reaction is described in detail below.

(a) The compound of the formula (XII) can be produced by reacting the compound of the formula (X) with the compound of the formula (XI) in the presence of a base and a solvent. The compound of the formula (XI) can be used in a proportion of 0.8 equivalent to large excess, desirably 1 to 30 equivalents, relative to 1 mol of the compound of the formula (X). Examples of the base include those similar to the reaction in the first half of the above production method [2]. A base can be used in the ratio of 1-5 equivalent with respect to 1 mol of compounds of Formula (X), desirably 1-2 equivalent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5]. Among them, ethers are desirable. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(b) The compound of the formula (XIII) can be produced by hydrolyzing the compound of the formula (XII) in the presence of a base and water. Examples of the base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. The base can be used in a proportion of 1 equivalent to a large excess with respect to the compound of the formula (XII). The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(c) The compound of the formula (XIV) can be produced by reacting the compound of the formula (XIII) with a halogenating agent in the presence of a solvent. Examples of the halogenating agent include thionyl chloride and oxalyl dichloride. The halogenating agent can be used in a proportion of 1 to 5 equivalents, desirably 1 to 2 equivalents, relative to 1 mol of the compound of the formula (XIII). Any solvent may be used as long as it is inert to the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.

(d) The 4,5-dihydro-5-oxo [1,2,4] triazolo [1,5-a] pyrimidine derivative of the formula (XV) is a compound of the formula (XIV) and a compound of the formula (V) Can be produced by condensation. The compound of the formula (V) can be used in a proportion of 0.8 to 10 equivalents, desirably 1 to 2.5 equivalents, relative to 1 mol of the compound of the formula (XIV). This reaction can usually be performed in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction. For example, the same reaction as in the first half of the above production method [5] can be mentioned, but acid amides are particularly desirable. The reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C. The reaction time is usually 0.5 to 100 hours.

(e) The 5-halo [1,2,4] triazolo [1,5-a] pyrimidine derivative of the formula (I-6) is produced by reacting the compound of compound (XV) with a halogenating agent. be able to. Examples of the halogenating agent include thionyl chloride, phosphorus oxychloride, phosphorus oxybromide and the like. The halogenating agent can be used in a proportion of 1 to 20 equivalents, preferably 1 to 8 equivalents, relative to 1 mol of the compound of the formula (XV). This reaction can usually be performed in the presence of a solvent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C. The reaction time is usually 0.1 to 24 hours.
Manufacturing method [7]

In the production process [7], R ⁹ , R ^1c , X and m are as described above.

  In the production method [7], the compound of formula (X) is reacted with the compound of formula (XVI) to obtain the compound of formula (IX), and the compound of formula (IX) and formula (V) The latter reaction consists of condensing the compound to obtain the [1,2,4] triazolo [1,5-a] pyrimidine derivative of formula (I-5).

Production method [7] In the first half of the reaction, the compound of the formula (XVI) can be used in a proportion of 0.8 equivalent to a large excess, preferably 1 to 10 equivalents, relative to 1 mol of the compound of the formula (X). This reaction can be performed in the presence of a base and a solvent. Examples of the base include those similar to the reaction in the first half of the above production method [5]. A base can be used in the ratio of 1-5 equivalent with respect to 1 mol of compounds of Formula (X), desirably 1-2 equivalent. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include those similar to the reaction in the first half of the above production method [5]. Among them, ethers are desirable. The reaction temperature is usually 0 to 70 ° C., preferably 10 to 50 ° C. The reaction time is usually 0.1 to 24 hours.
The reaction in the latter half of the production process [7] can be carried out in the same manner as the reaction in the latter half of the production process [5]. Manufacturing method [8]

In the production process [8], R ¹¹ and R ¹² are each independently hydrogen, alkyl or cycloalkyl; X, Y and m are as described above.

  In the production method [8], the compound of the formula (I-7) and the halogenating agent are reacted in the presence of a solvent and a small amount of a radical initiator to thereby produce [1,2,4 of the formula (I-8). ] A triazolo [1,5-a] pyrimidine derivative can be produced. This reaction can be performed under light irradiation as needed.

Examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like. The halogenating agent can be used in a proportion of 1 to 5 equivalents, preferably 1 to 2 equivalents, relative to the compound of formula (I-7). Examples of the radical initiator include benzoyl peroxide and azobisisobutyronitrile. Any solvent may be used as long as it is inert to the reaction. Examples thereof include halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane. The reaction temperature is usually 0 to 100 ° C, preferably 10 to 80 ° C. The reaction time is usually 0.1 to 24 hours.
Manufacturing method [9]

In the production process [9], R ¹³ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl, heterocyclic group optionally substituted with alkyl, OR ¹⁴ , SR ¹⁴ or NR ¹⁵ R ¹⁶ , wherein R ¹⁴ , R ¹⁵ and R ¹⁶ are each independently alkyl substituted with A, substituted with A Cycloalkyl, which may be substituted, alkenyl which may be substituted with A, or alkynyl which may be substituted with A; R ¹¹ , R ¹² , A, X and m are as defined above.

  In the production method [9], the compound of the formula (I-8) and the nucleophile are reacted in the presence of a solvent to produce [1,2,4] triazolo [1,5- a] Pyrimidine derivatives can be produced.

  Examples of nucleophiles include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal haloalkoxides such as sodium trifluoromethyl ethoxide; alkali metal mercaptides such as sodium methyl mercaptan; methylamine and dimethylamine Primary or secondary amines such as pyridine, piperidine, morpholine; organometallic reagents such as methylmagnesium bromide, ethylmagnesium bromide, phenylmagnesium bromide; fluorine such as potassium fluoride, cesium fluoride, tetrabutylammonium fluoride A cyanating agent such as potassium cyanide and sodium cyanide; and the like. The nucleophilic reagent can be used at a ratio of 1 to 5 equivalents, desirably 1 to 3 equivalents, per 1 mol of the compound of formula (I-8). The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same ones as in the reaction of the above production method [4]. The reaction temperature is usually −100 to 50 ° C., preferably −70 to 20 ° C. The reaction time is usually 6 to 48 hours.

  Among the above-mentioned production methods, production method [1], production method [5] or production method [7] is a particularly desirable embodiment.

  The desirable aspect of the pest control agent containing this invention compound is described below. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.

  Pesticides for agricultural and horticultural use are useful, for example, as insecticides, acaricides, nematicides or soil insecticides. Plant parasitic mites such as rustic mites, mites, aphids such as peach aphids and cotton aphids; diamondback moths, weevil, scallops, codling moths, ball worms, tobacco worms, mai moths, yellow moths, prickly winged clams, Colorado Agricultural pests such as leaf beetle, cucumber beetle, ball weevil, planthoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, Tamanayaga, Kaburayaga, ants, etc .; Parasitic nematodes such as mosquitoes, cyst nematodes, nesting nematodes, rice scented nematodes, strawberry nematodes, pine wood nematodes, etc .; gastropods such as slugs, maimai, etc .; Soil pests such as legumes; hygiene pests such as house dust mites, cockroaches, house flies, and mosquitoes; storage pests such as bark moths, azuki beetles, mosquito moths, bark beetles, etc .; It is effective for the control of clothing such as mosquitoes, house pests; indoor dust mites such as mite, mite, mite. The agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is most useful as an insecticidal or acaricidal agent because it exhibits a further excellent effect in controlling plant parasitic mites and agricultural pests. Moreover, the agricultural and horticultural pesticide containing the compound of the present invention is also effective for controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, and synthetic pyrethroid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.

  Another desirable embodiment of the pest control agent containing the compound of the present invention is a farm that comprehensively controls the aforementioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests, etc. Examples include horticultural pest control agents.

  The agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, by mixing the compound with various agricultural adjuvants, Used in various forms such as oil suspensions, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. It can be in any formulation form. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water , Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol, etc .; fatty acid salts , Benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfate esters, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol ether sulfates, alcohol sulfates Acid ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester, alkyl aryl phosphate, styryl aryl Phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate , Anionic surfactants such as naphthalenesulfonic acid formalin condensate salts; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides, fatty acid esters Cole polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid Nonionic surfactants such as esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid esters; olive oil, kapok oil, castor oil, palm oil, straw oil , Palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, cutting oil Vegetable oil or mineral oil such as liquid paraffin; and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the art. For example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction. Various commonly used adjuvants such as agents, antifungal agents and the like can also be used. The compounding ratio of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  The application of the agricultural and horticultural pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence status, but generally 0.05 to 800,000 ppm, The active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g, of the present compound per hectare. In addition, application of the agricultural and horticultural pest control agent, which is another desirable embodiment of the pest control agent containing the compound of the present invention, is performed according to the application of the pest control agent. The present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

  Application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, spraying, misting, atomizing, It can be carried out by powder application, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra low volume application method (ultra low volume). In this method, it is possible to contain 100% of the active ingredient.

  In addition, the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. There is. Other agrochemicals include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. In particular, a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together. The present invention includes such a composition for controlling mixed pests.

  The mixing ratio between the compound of the present invention and the active ingredient compound of other agricultural chemicals cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, but generally 1: 300 to 300: 1, preferably 1: 100 to 100: 1. In addition, the appropriate amount to be applied is 0.1 to 50000 g, preferably 1 to 30000 g as the total active ingredient compound amount per hectare. The present invention also includes a method for controlling pests by a method for applying such a composition for controlling mixed pests.

Examples of active ingredient compounds (generic name; including some pending applications or test codes) of pesticides, acaricides, nematicides or soil pesticides in the above other pesticides include, for example, profenofos , Dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fothiaz , Cadusafos, dislufoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulfophos ( sulprofos), thiometon, bamidthione (vamidot) hion), pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlovinphos, chlorfen Chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, Parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos ( terbufos), phospamidon (phospa organophosphate compounds such as midon, phosmet, phorate;
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocab, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicohol, tetradifon, endosulufan, dienochlor, dieldrin;

Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrin, esfenvalerate, Tetramethrin, resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermethri n), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta cypermethrin ( pyrethroid compounds such as beta-cypermethrin, beta-cyfluthrin, metofluthrin, phenothrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, novaluron, ), Bistrifluron, benzoylurea compounds such as fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, fenoxycarb, diofenolan;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, etiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Neonicochioids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, nithiazine;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;

Pyridine compounds such as pyridaryl, flonicamid and the like;
Tetronic acid compounds such as spirodiclofen;
Strobilurin-based compounds such as fluacrypyrim;
Pyridinamine compounds such as flufenerim;
Dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds such as buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, spiromesifen, spirotetramat, propargi Propargite, clofentezine, metaflumizone, flubendiamide, cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon, pirafluquinazon ), Pyridaben, amidoflumet, chlorobenzoate, sulfluramid, hydramethylnon, metaldehyde, HGW 86, ryanodine, etc .; Is mentioned. Furthermore, Bacillus thuringienses aizawai, Bacillus thuringienses kurstaki, Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses tenebrionis, crystalline protein toxins produced by Bacillus thuringienses, entomopathogenic fungi, nematode pathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin and antibiotics such as abamectin and emamectin; natural products such as azadirachtin and rotenone; repellents such as deet;

Examples of the bactericidal active ingredient compounds (generic name; including partial application, or Japan Plant Protection Association test code) in the above-mentioned other agricultural chemicals include, for example, mepanipyrim, pyrimethanil, cyprodinil ( anilinopyrimidine compounds such as cyprodinil);
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole, ipconazole ), Azole compounds such as imibenconazole;

Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Phenylamide compounds such as furalaxyl, cyprofuram;

Sulfenic acid compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetylaluminum (fosetyl-Al), turfosfos-methyl, edifenphos, iprobenfos, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, Organophosphorus compounds such as aluminum ethyl hydrogen phosphonate;
N-halogenothioalkyl compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;

Benzanilide compounds such as flutolanil, mepronil, zoxamid, tiadinil;
Anilide compounds such as carboxin, oxycarboxin, thifluzamide, penthiopyrad, boscalid;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol, flutriafol;
Piperidine compounds such as fenpropidine;
Morpholine compounds such as fenpropimorph, spiroxamine, tridemorph;

Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin, fluacrypyrin;

Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Silylamide compounds such as silthiopham;
Amino acid amide carbamate compounds such as iprovalicarb, benchthiavalicarb-isopropyl;
Imidazolidine compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamid;
Phenoxyamide compounds such as fenoxanil;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine;

  Other compounds include isoprothiolane, Pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, metam sodium salt ( metam-sodium, nicobifen, metrafenone, MTF-753, UBF-307, diclocymet, proquinazid, amisulbrom (aka amibromdole), pyribencarb Syngenta 446510 (mandipropamid, dipromandamid), fluopicolide, carpropamid, BCF051, BCM061, BCM062; and the like.

  Other pesticides that can be used in combination with or combined with the compounds of the present invention include, for example, active ingredient compounds of herbicides such as those described in the Farm Chemicals Handbook (2002 edition), especially those of soil treatment type. is there.

  Examples of animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). , Vascular, subcutaneous, lymphoid tissue, etc.) are effective in controlling endoparasites, and in particular, are effective in controlling ectoparasites.

  Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis megaspinosa ), tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres cati ; mite mites like Demodex canis , and the like. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

Examples of fleas include ectoparasite insects belonging to the order Flea ( Siphonaptera ), and more specifically, fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ) and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mouse minnow ( Nosopsyllus fasciatus ), and Yamato mouse minnow ( Monopsyllus anisus ). Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas, cat fleas and the like.

  Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke like liver fluke; coccidium, malaria parasite, intestinal granulocyst, toxoplasma Protozoa such as Ptosporidium, and the like.

  Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cows or horses.

  When the compound of the present invention is used as an animal parasite control agent, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aquatic suspensions, It can also be used in various forms such as an oily suspension. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the above-mentioned preparation adjuvants for agricultural and horticultural pest control agents; positive agents such as cetyltrimethylammonium bromide. Ionic surfactants: water, acetone, acetonitrile, monomethylacetamide, dimethylacetamide, dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, ethanol, isopropanol, benzyl alcohol, ethylene glycol, Propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, die Solvents such as tylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; antioxidants such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Agents; film forming agents such as polyvinyl pyrrolidone, polyvinyl alcohol, copolymers of vinyl acetate and vinyl pyrrolidone; vegetable oils and mineral oils exemplified as preparation aids for the aforementioned agricultural and horticultural pest control agents; lactose, sucrose, glucose, Starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed materials; Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also

  The mixing ratio of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

  Administration of the compound of the present invention to the host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention. As a parenteral administration method, for example, the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on For example, a method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.

  The dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 kg body weight of the host animal. Is suitable for administration.

  The present invention also includes a method for controlling pests by the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.

  Further, in the present invention, by controlling animal parasitic pests as described above, there are cases where various diseases of host animals caused by them can be prevented or treated. As described above, the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.

  When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, It can be mixed with or used in combination with preservatives and the like. Also, if necessary, mix or use with other animal drugs and pesticides such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited. The present invention includes a composition for controlling mixed pests in which various components as described above are mixed or used together, and a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. Is also included.

Desirable embodiments of the compound of the formula (I) are as follows. However, the present invention is not limited to these.
(1) A pyridyl-triazolopyrimidine derivative represented by the formula (I) or a salt thereof.
(2) R ¹ is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, aryl , a heterocyclic ^{group, oR 2, S (O)} n R 3 or be a NR ⁴ R ^5; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl or aryl; R ³ is alkyl; R ⁵ is Hydrogen or alkyl; A is halogen, OR ² , S (O) _n R ³ , NR ⁴ R ⁵ , cyano, cycloalkyl, aryl or heterocyclic group; X is alkyl, alkenyl, alkynyl, halogen, haloalkyl The pyridyl-triazolopyrimidine derivative or a salt thereof according to (1), which is cyano or nitro.
(3) The above (2), wherein R ¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, halogen, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ Or a salt thereof.
(4) The pyridyl-triazolo according to (3), wherein R ¹ is hydrogen, alkyl, haloalkyl, alkynyl, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ^5. A pyrimidine derivative or a salt thereof.
(5) R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, aryl, complex The pyridyl-triazolopyrimidine derivative or a salt thereof according to (2) above, which is a cyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ .
(6) The pyridyl according to (5), wherein R ¹ is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ^5. A triazolopyrimidine derivative or a salt thereof.
(7) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (6), wherein R ¹ is alkyl, haloalkyl, cycloalkyl or alkenyl.
(8) The pyridyl-triazolopyrimidine derivative according to (5), wherein R ¹ is alkyl, haloalkyl, alkynyl, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ^5. Or a salt thereof.
(9) The pyridyl-triazolopyrimidine derivative or the salt thereof according to (8), wherein R ¹ is alkyl, haloalkyl, alkynyl, cyano, aryl, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ .
(10) The pyridyl-triazolopyrimidine derivative or the salt thereof according to (9), wherein R ¹ is alkyl, trifluoromethyl, alkynyl, cyano, phenyl, alkoxy, alkylthio, alkylsulfonyl, dialkylamino, or amino.
(11) The pyridyl-triazolopyrimidine derivative or a salt thereof according to (2), wherein X is alkyl, alkynyl, halogen, haloalkyl, cyano or nitro.

  Next, examples of the present invention will be described, but the present invention is not limited thereto. First, the synthesis example of this invention compound is described.

Synthesis Example 1 Synthesis of 7- (3-bromo-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 4)
(1) 728 mg of 2-acetyl-3-bromo-5- (trifluoromethyl) pyridine and 466 mg of N, N-dimethylformamide dimethylacetal were reacted at 100 ° C. for 16 hours in 5 ml of toluene. The reaction solution was concentrated under reduced pressure to give 1- (3-bromo-5- (trifluoromethyl) pyridin-2-yl) -3- (dimethylamino) -2-propen-1-one (intermediate No. IV described later). -7) 866 mg was obtained.
(2) 866 mg of 1- (3-bromo-5- (trifluoromethyl) pyridin-2-yl) -3- (dimethylamino) -2-propen-1-one obtained in (1) was added to 10 ml of acetic acid. After dissolution, 225 mg of 3-amino-1H-1,2,4-triazole was added and heated to reflux for 7 hours. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/2) to obtain 402 mg of the desired product.

Synthesis Example 2 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 19) Synthesis of
(1) 2-acetyl-3-chloro-5- (trifluoromethyl) pyridine (1.0 g) and N, N-dimethylacetamide dimethylacetal (715 mg) were reacted in toluene (6 ml) at 100 ° C. for 14 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 1- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) -3. 869 mg of-(dimethylamino) -2-buten-1-one (intermediate No. IV-1 described later) was obtained.
(2) 850 mg of 1- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) -3- (dimethylamino) -2-buten-1-one obtained in (1) was added to 3 ml of acetic acid. After dissolution, 244 mg of 3-amino-1H-1,2,4-triazole was added and the mixture was heated to reflux for 17 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 609 mg of the desired product.

Synthesis Example 3 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) 5- (trifluoromethyl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. .20)
(1) To a solution of 1 g of 2-acetyl-3-chloro-5- (trifluoromethyl) pyridine and 635 mg of ethyl 2,2,2-trifluoroacetate in 9 ml of tetrahydrofuran (dehydrated) was added 608 mg of a 21% ethanol solution of sodium ethoxide. The mixture was added at 0 ° C. and stirred at room temperature for 13 hours. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 1- (3-chloro-5- (trifluoromethyl) pyridine-2- Yl) -4,4,4-trifluorobutane-1,3-dione (intermediate No. IX-25 described later) 1.4 g was obtained.
(2) 9 ml of acetic acid solution of 1- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) -4,4,4-trifluorobutane-1,3-dione obtained in (1) To this was added 376 mg of 3-amino-1H-1,2,4-triazole, and the mixture was heated to reflux for 6 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 4/1) to obtain 111 mg of the desired product.

Synthesis Example 4 Synthesis of 5- (methylthio) -7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 21)
(1) To 55 ml of tetrahydrofuran (dehydrated), 3.68 g of potassium t-butoxide and 3.1 g of 2-acetyl-5- (trifluoromethyl) pyridine were added and stirred at room temperature. Ten minutes later, 1.37 g of carbon disulfide and 4.9 g of methyl iodide were sequentially added, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 9/1) and 3,3-bis (methylthio) -1- (5- (trifluoromethyl) pyridin-2-yl) 3.0 g of 2-propen-1-one was obtained.
(2) 3,3-bis (methylthio) -1- (5- (trifluoromethyl) pyridin-2-yl) -2-propen-1-one obtained in (1) 2.7 g of N-methyl To a 30 ml solution of pyrrolidinone, 1.16 g of 3-amino-1H-1,2,4-triazole and 2.5 g of potassium carbonate were added and stirred at 150 ° C. for 30 minutes. After completion of the reaction, the reaction solution was returned to room temperature, water was added to the reaction solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 4/1) to obtain 600 mg of the desired product.

Synthesis Example 5 5- (methylsulfonyl) -7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 22) Synthesis 5- (methylthio) -7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine in 120 ml of chloroform was added to m-chloroperoxide. 700 mg of benzoic acid was added and heated to reflux for 2 hours. After completion of the reaction, the reaction solution was returned to room temperature, 1N aqueous sodium hydroxide solution was added to the reaction solution, extracted with chloroform, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 420 mg of the desired product.

Synthesis Example 6 Synthesis of 5-methoxy-7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 25) 5- (Methylsulfonyl) -7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine in 100 ml of methanol in 28 ml of sodium methoxide 62 mg of methanol solution was added and stirred at room temperature for 5 minutes. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 85 mg of the desired product.

Synthesis Example 7 Synthesis of 5-phenyl-7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 28) 5- (Methylsulfonyl) -7- (5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine in 200 mg of tetrahydrofuran (dehydrated) in 3 ml of phenylmagnesium bromide 0.2 ml of a 3.0 M tetrahydrofuran solution was added at 0 ° C., and the mixture was stirred at 0 ° C. for 5 minutes. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 4/1) to obtain 93 mg of the desired product.

Synthesis Example 8 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) -5-cyclopropyl- [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 82) ) Synthesis
(1) 805 mg of sodium ethoxide was added to a solution of 2 g of ethyl-3-chloro-5- (trifluoromethyl) pyridine-2-carboxylate and 3.4 g of cyclopropyl methyl ketone in 15 ml of tetrahydrofuran (dehydrated), Stir at room temperature for 10 minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 1- (3-chloro- It was confirmed by ¹ H-NMR that 5- (trifluoromethyl) pyridin-2-yl) -cyclopropylpropane-1,3-dione (intermediate No. IX-18) was contained.
(2) 15 ml of acetic acid and 730 mg of 3-amino-1H-1,2,4-triazole were added to the total amount of the liquid obtained in (1), and the mixture was stirred at 100 ° C. overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 4/1) to obtain 1.67 g of the desired product.

Synthesis Example 9 7- (3-Bromo-5- (trifluoromethyl) pyridin-2-yl) -5-isopropyl- [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 95) Synthesis of
(1) 408 mg of sodium ethoxide was added to a solution of 1.2 g of ethyl-3-bromo-5- (trifluoromethyl) pyridine-2-carboxylate and 1.73 g of isopropyl methyl ketone in 13 ml of tetrahydrofuran (dehydrated) at room temperature. For 15 minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give 1- (3-bromo-5- (trifluoromethyl). ) Pyridin-2-yl) -4-methylpentane-1,3-dione (Intermediate No. IX-22) was obtained.
(2) To the total amount of the liquid obtained in (1), 8 ml of acetic acid and 370 mg of 3-amino-1H-1,2,4-triazole were added and stirred at 100 ° C. overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1) to obtain 650 mg of the desired product.

Synthesis Example 10 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) -5-ethyl- [1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 16) Synthesis of
(1) To a solution obtained by dissolving 6.0 g of ethyl-3-chloro-5- (trifluoromethyl) pyridine-2-carboxylate and 2.6 g of methyl ethyl ketone in 80 ml of tetrahydrofuran (dehydrated), 3.2 g of sodium ethoxide was added and room temperature was added. For 15 minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 1- (3-chloro- It was confirmed by ¹ H-NMR that 5- (trifluoromethyl) pyridin-2-yl) -pentane-1,3-dione (intermediate No. IX-7) was contained.
(2) To the total amount of the liquid obtained in (1), 65 ml of acetic acid and 2.2 g of 3-amino-1H-1,2,4-triazole were added and stirred at 100 ° C. overnight. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added to the resulting residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 3/1) to obtain 3.1 g of the desired product.

Synthesis Example 11 5- (1-Bromoethyl) -7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (compound Synthesis of No. 101) 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) -5-ethyl- [1,2,4] triazolo [1,5-a] pyrimidine 5.76 g Was dissolved in 30 ml of chloroform, 4.47 g of N-bromosuccinimide and 50 mg of azobisisobutyronitrile (AIBN) were added, and the mixture was stirred overnight with heating under reflux. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 5/2) to obtain 4.47 g of the desired product as a solid.

Synthesis Example 12 5-Bromomethyl-7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine (Compound No. 60) Synthesis of 7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) -5-methyl- [1,2,4] triazolo [1,5-a] pyrimidine in 3 ml of carbon tetrachloride To the dissolved solution, 3 mg of N-bromosuccinimide and 13 mg of azobisisobutyronitrile (AIBN) were added, and the mixture was stirred overnight with heating under reflux. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 7/3) to obtain 86 mg of the desired product.

Synthesis Example 13 7- (3-Chloro-5- (trifluoromethyl) pyridin-2-yl) -5-((2,2,2-trifluoroethoxy) methyl)-[1,2,4] triazolo [ Synthesis of 1,5-a] pyrimidine (Compound No. 63) After adding 230 mg of 2,2,2-trifluoroethanol to 8 ml of a solution of 33% 60% sodium hydride in tetrahydrofuran (dehydrated), the mixture was stirred at room temperature for 5 minutes. -300 mg of bromomethyl-7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine was added and stirred for 5 minutes. After completion of the reaction, the reaction mixture was acidified with 1N hydrochloric acid, extracted with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 1/1) to obtain 97 mg of the desired product.

Representative examples of the compounds of formula (I) are listed in Table 1. These compounds can be synthesized based on the above synthesis examples or various production methods of the compound of the present invention described above. In Table 1, No. indicates the compound No., Me is methyl, Et is ethyl, n-Pr is normal propyl, i-Pr is isopropyl, n-Bu is normal butyl, and t-Bu is Tertiary butyl, sec-Bu is secondary butyl, Ac is acetyl, Ph is phenyl, and the temperatures shown as physical properties are melting points. Table 2 shows ¹ H-NMR for some of the compounds of formula (I).

Representative examples of the compound of the formula (IV) in the production method [1] are listed in Table 3. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Table 3, No. represents intermediate No., Me represents methyl, Et represents ethyl, n-Pr represents normal propyl, and the temperatures indicated as physical properties are melting points. Table 4 shows ¹ H-NMR for some of the compounds of formula (IV).

Table 5 shows representative examples of the compound of formula (IX) in the above production method [5] or production method [7]. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Table 5, No. indicates intermediate No., Me is methyl, Et is ethyl, i-Pr is isopropyl, i-Bu is isobutyl, t-Bu is tertiary butyl, sec-Bu Represents secondary butyl, Ph represents phenyl, and the temperature indicated as a physical property is the melting point. Table 6 shows ¹ H-NMR for some of the compounds of the formula (IX).

Next, test examples are described.
Test Example 1 Effect test on peach aphid Japanese radish leaves were inserted into a test tube containing water, and about 20 first-instar larvae were released on the leaves. The next day, after counting the number of larvae parasitic on the radish leaves, the parasitic radish leaves were immersed in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm for about 10 seconds. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality rate was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. Tests with Compound Nos. 4, 15, 16, 17, 18, 19, 20, 41, 43, 44, 48, 51, 53, 68, 73, 78, 79, 80, 82, 94, 95, and 104 As a result, all the compounds showed a death rate of 90% or more.
Death rate (%) = (1− (number of surviving insects / number of treated insects)) × 100

Test Example 2 Effect test on green planthopper Rice seedlings were immersed for about 10 seconds in a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. Ten 10-year-old larvae were released into this, and the tube mouth was covered with gauze and left in a constant temperature room at 25 ° C. Five days after the insect release, the dead planthopper was judged to be alive or dead, and the mortality rate was determined by the following formula. Compound No. 4, 12, 15, 16, 17, 19, 20, 41, 43, 44, 48, 52, 57, 68, 70, 75, 79, 80, 81, 82, 83, 87, 89, When 91, 94, 95, 98, 99, 104, 105 and 107 were tested, all the compounds showed a death rate of 90% or more.
Death rate (%) = (Number of dead insects / Number of dead insects) × 100

Test Example 3 Effect test on silver leaf whitefly A potted cucumber seedling infested with silver leaf whitefly 1-2 instar larvae was sprayed with a chemical solution prepared so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control efficiency (%) was determined by the following formula. When the compound Nos. 4, 5, 12, 14, 15, 16, 17, 18, 19, 20, 44, 48, 80, 82 and 94 were tested, all the compounds had a control efficiency of 80% or more. Indicated.

Control efficiency (%) = (1− (Ta × Cb) / (Tb × Ca)) × 100
Ta: old larvae after treatment in treated cucumber seedlings
Tb: Number of 1-2 instar larvae before treatment in treated cucumber seedlings
Ca: number of old larvae after treatment in untreated cucumber seedlings
Cb: Number of larvae 1 to 2 instar before treatment in untreated cucumber seedlings

Test Example 4 Medicinal Efficacy Test Using Dogs Against Phytophyllum Tick A dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention. Let go through and artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of the present invention drops or kills the parasitic spider mite.

Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea A gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. After the treatment, the fleas are collected using a flea removal comb and the number of fixings is counted. As a result, the compound of the present invention suppresses flea infestation.

Next, formulation examples are described.
Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalene sulfonate 2 parts by weight or more To make a wettable powder.

Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) Talc 60 parts by weight (3) Calcium carbonate 34.5 parts by weight (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.

Formulation Example 3
(1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the present compound Mix at a weight ratio of 4: 1 to make a wettable powder.

Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are uniformly mixed in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.

Formulation Example 7
(1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).

Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 part by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) 80 parts by weight of diethylene glycol monoethyl ether (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain an aqueous solution.

Claims (16)

Formula (I):

[Wherein, R ¹ is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl, heterocyclic group optionally substituted with alkyl, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ ; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl or aryl R ³ is alkyl or acetyl; R ⁴ is hydrogen or alkyl; R ⁵ is hydrogen, alkyl, acetyl, CH ₂ CH ₂ OR ² or CH ₂ CN; A is halogen, OR ² , ^{_{S (O) n R 3,}} NR 4 R 5, cyano, alkyl, cycloalkyl, aryl, heterocyclic group, an SCH ₂ COOR ² or -CH (CN) _2; X is alkyl, alkenyl, Rukiniru, aryl, halogen, haloalkyl, cyano, ^{nitro, NR 4 R 5, S (} O) be _n R ^3, COR ² or COOR ^2; m is an integer of from 1 to 4; n is integer of 0 to 2 Provided that 7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine is excluded] A triazolopyrimidine derivative or a salt thereof. R ¹ is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, aryl, heterocyclic The group OR ² , S (O) _n R ³ or NR ⁴ R ⁵ ; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl or aryl; R ³ is alkyl; R ⁵ is hydrogen or alkyl A is halogen, OR ² , S (O) _n R ³ , NR ⁴ R ⁵ , cyano, cycloalkyl, aryl or heterocyclic group; X is alkyl, alkenyl, alkynyl, halogen, haloalkyl, cyano or The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1, which is nitro. The pyridyl according to claim 2, wherein R ¹ is hydrogen, alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, halogen, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ^5. A triazolopyrimidine derivative or a salt thereof. The pyridyl-triazolopyrimidine derivative according to claim 3, wherein R ¹ is hydrogen, alkyl, haloalkyl, alkynyl, cyano, aryl, heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ^5. salt. R ¹ is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, aryl, heterocyclic group, _{^{oR 2, S (O) n}} R 3 or NR ⁴ R ⁵ is pyridyl as defined in claim 2 - triazolopyrimidine derivative or a salt thereof. R ¹ is alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl, cyano, aryl, heterocyclic ^{group, OR 2, S (O)} n R 3 or pyridyl according to claim 5 NR a ⁴ R ⁵ - triazolopyrimidine Derivatives or salts thereof. The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 6, wherein R ¹ is alkyl, haloalkyl, cycloalkyl or alkenyl. The pyridyl-triazolopyrimidine derivative or a salt thereof according to claim ⁵ , wherein R ¹ is alkyl, haloalkyl, alkynyl, cyano, aryl, a heterocyclic group, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ . A pest control agent comprising the pyridyl-triazolopyrimidine derivative of claim 1 or a salt thereof as an active ingredient. An agricultural and horticultural pest control agent comprising the pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1 as an active ingredient. An insecticide, acaricide, nematicide or soil insecticide containing the pyridyl-triazolopyrimidine derivative or salt thereof of claim 1 as an active ingredient. An insecticide or acaricide containing the pyridyl-triazolopyrimidine derivative of claim 1 or a salt thereof as an active ingredient. A method for controlling pests by applying an effective amount of the pyridyl-triazolopyrimidine derivative or a salt thereof according to claim 1. Formula (I):

[Wherein, R ¹ is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, halogen, cyano, Aryl, heterocyclic group optionally substituted with alkyl, OR ² , S (O) _n R ³ or NR ⁴ R ⁵ ; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl or aryl R ³ is alkyl or acetyl; R ⁴ is hydrogen or alkyl; R ⁵ is hydrogen, alkyl, acetyl, CH ₂ CH ₂ OR ² or CH ₂ CN; A is halogen, OR ² , ^{_{S (O) n R 3,}} NR 4 R 5, cyano, alkyl, cycloalkyl, aryl, heterocyclic group, an SCH ₂ COOR ² or -CH (CN) _2; X is alkyl, alkenyl, Rukiniru, aryl, halogen, haloalkyl, cyano, ^{nitro, NR 4 R 5, S (} O) be _n R ^3, COR ² or COOR ^2; m is an integer of from 1 to 4; n is integer of 0 to 2 Provided that 7- (3-chloro-5- (trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine is excluded] A method for producing a triazolopyrimidine derivative or a salt thereof,
(1) Formula (IV):

[Wherein, X and m are as defined above, R ^1a is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, substituted with A An alkynyl, aryl or alkyl which may be substituted, and R ⁷ is alkyl], an α, β-unsaturated ketone derivative represented by formula (V):

Or a compound represented by
(2) Formula (VII):

[Wherein R ³ , X and m are as defined above] or an α, β-unsaturated ketone derivative represented by the formula (V),
(3) Formula (I-2):

[Wherein R ³ , X and m are as defined above] or a compound represented by
(4) Formula (I-3)

[Wherein R ³ , X and m are as defined above and na is an integer of 1 to 2] and a nucleophile is reacted,
(5) Formula (IX):

[Wherein, X and m are as defined above, R ^1c is alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, substituted with A Or a heterocyclic group which may be substituted with alkynyl, aryl or alkyl, and a compound of the above formula (V), or (6) formula (XV):

[Wherein X and m are as defined above] halogenating a 4,5-dihydro-5-oxo [1,2,4] triazolo [1,5-a] pyrimidine derivative represented by A method for producing a pyridyl-triazolopyrimidine derivative of the above formula (I) or a salt thereof, Formula (I-1):

Wherein R ^1a is hydrogen, alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, aryl or alkyl An optionally substituted heterocyclic group; X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , S (O) _n R ³ , COR ² or COOR ² ; R ² is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl or aryl; R ³ is alkyl or acetyl; R ⁴ is hydrogen or alkyl; R ⁵ is hydrogen, alkyl, acetyl, CH It is ₂ CH ₂ oR ² or CH ₂ CN; A is ^{halogen, oR 2, S (O)} n R 3, NR 4 R 5, cyano, alkyl, cycloalkyl Aryl, heterocyclic group, an SCH ₂ COOR ² or -CH (CN) _2; m is an integer of from 1 to 4; n is an integer from 0 to 2; provided, 7- (3-chloro-5 -(Trifluoromethyl) pyridin-2-yl)-[1,2,4] triazolo [1,5-a] pyrimidine is excluded], and a method for producing a pyridyl-triazolopyrimidine derivative represented by the following formula: Formula (II):

[Wherein X and m are as defined above], and the formula (III):

[Wherein R ^1a is as defined above; R ⁶ and R ⁷ are each independently alkyl] and condensed with a compound of formula (IV):

[Wherein R ^1a , R ⁷ , X and m are as defined above], an α, β-unsaturated ketone derivative represented by formula (V):

A method for producing the pyridyl-triazolopyrimidine derivative or a salt thereof, wherein the compound is condensed with a compound represented by the formula: Formula (I-5):

[Wherein, R ^1c is substituted with alkyl optionally substituted with A, cycloalkyl optionally substituted with A, alkenyl optionally substituted with A, alkynyl optionally substituted with A, aryl or alkyl. X is alkyl, alkenyl, alkynyl, aryl, halogen, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , S (O) _n R ³ , COR ² or COOR ² ; R ² Is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxyalkyl, acetyl or aryl; R ³ is alkyl or acetyl; R ⁴ is hydrogen or alkyl; R ⁵ is hydrogen, alkyl, acetyl, CH ₂ CH ₂ be oR ² or CH ₂ CN; A is ^{halogen, oR 2, S (O)} n R 3, NR 4 R 5, cyano, alkyl, cycloalkyl, Ali Le, heterocyclic group, an SCH ₂ COOR ² or -CH (CN) _2; m is an integer of from 1 to 4; n is pyridyl represented by a is] an integer of 0 to 2 - triazolopyrimidine derivative Or a method of producing a salt thereof,
(1) Formula (II):

[Wherein X and m are as defined above], and the formula (VIII): R ^1C CO ₂ R ^{8 wherein} R ^1c is as defined above; R ⁸ is alkyl Or a compound represented by
(2) Formula (X):

[Wherein X and m are as defined above; R ⁹ is alkyl], and a compound represented by formula (XVI)

[Wherein R ^1c is as defined above] is reacted with a compound represented by formula (IX):

[Wherein R ^1c , X and m are as described above]
(3) the compound of formula (IX) and formula (V):

A method for producing the pyridyl-triazolopyrimidine derivative or a salt thereof, wherein the compound is condensed with a compound represented by the formula: